


The Guessing Game

by Anonymous



Category: Supernatural
Genre: Blindfolds, Bondage, Bottom Castiel (Supernatural), M/M, Multi, Object Insertion, Pain Kink, Spanking, WinCasWin
Language: English
Status: Completed
Published: 2019-06-22
Updated: 2019-06-22
Packaged: 2020-05-16 13:02:23
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,495
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19318735
Author URL: https://archiveofourown.org/
Summary: If Cas can guess what Dean is using on him, then he gets to come.If he doesn’t, then he doesn’t, but Cas is an extremely sneaky angel and the brothers should probably remember that.





	The Guessing Game

**Author's Note:**

> It does seem in the story that Cas is struggling with what the brothers are doing to him and it is intense for him, but he doesn’t safeword and Dean and Sam are making sure he’s okay.

Cas whined when Dean kissed him, keeping it chaste, barely brushing the angel’s lips with his own.

He pulled back, and Cas tried to follow, but the leather cuffs around his wrists, attached to the headboard, kept him in check.

Cas slumped back, on edge and desperate, not helped by the blindfold covering his eyes. “Please,” he moaned.

Sam was half hard just from watching. 

They had Cas completely naked, knees bent, legs tied open, and pretty soon they’d be giving him more attention that he could handle.

Well, one part of him specifically, and Sam couldn’t wait.

“You know the rules, Cas,” he said. “If you can guess what we brought home for you, then you get to come.”

_On our dicks_ , he added, privately, being sure not to send that to Cas as an unintended prayer. _But you’ll get to come_.

And if he didnt…. Well.

Sam looked at Dean. His brother had a basin of hot soapy water set up on the nearby unit, and when he’d thoroughly cleaned their new ‘toy’ he dried it up and brought it over to Sam.

The younger brother nodded. Yeah, their angel was going to feel this.

“Might want to hold his hips,” Dean said. “In case he decides to be naughty.”

“I won’t,” Cas protested. “I promise, I won’t.”

Sam grinned. He kind of hoped Cas would, because it had been a while since he’d earned himself a good spanking. Still, looking at what they were about to use on him, he had a feeling Cas’s ass would be red before they all went to sleep tonight.

“We’ll see,” he said, and then knelt over Cas’s hips, using his weight to pin them down.

It meant he couldn’t see Cas’s face, like this, but the angel had a safeword and Sam would turn around periodically to make sure Cas was okay.

Dean had settled between Cas’s legs, and was lubing their little present up to make sure it went in. Hell, it wouldn’t go easily, no matter how much lube Dean covered it in, but they didn’t want it to be impossible.

“Here we go,” Dean said, and pushed the narrow bowl of the candlestick into Cas’s hole.

The angel yelped, and only Sam’s weight kept him still.

Dean paused, letting Cas get used to the intrusion, before pushing it in a little further.

“Dean, Sam, wait…. It’s too...It hurts!”

Dean patted Cas’s thigh, soothingly, but then he pushed the candlestick in another half inch.

They’d been on a hunt the week before, interviewing the owner of a small antique shop (privately, they brothers had thought it was basically a junk shop passing itself off as something else) when they’d spotted the candlestick.

Missing its pair, it was ten bucks, and the brothers had been determined to take it home with them. This was part of the game, finding something new to torment Cas with.

The angel loved it, and sometimes he would even pick out an item he wanted them to use.

But Sam was sure Cas would never guess what they were pushing in him just now.

Behind him, Cas was panting hard as Dean worked the candlestick further into his hole. It was smooth the first inch and a half, but then it flared out into a knobbled bulge and Cas almost reared up when Dean started pressing that part inside him.

“No,” he gasped. “Please, please, Dean, Sam…”

Sam glanced behind him. Cas’s mouth was wide open, fingers clenched tight around the leather binding him. 

He signalled for Dean to hold up, and then looked back at the angel. 

“Cas. You safewording?”

After a moment, Cas seemed to have himself under control, and stubbornly shook his head. 

Sam motioned for Dean to continue, and grinned as Dean pressed a teasing kiss to the tip of Cas’s dick.

Still, Cas’s body resisted as Dean went back to pushing, but then it swallowed up the middle of the candlestick and that left a good three to four inches to the base.

That didn’t go easy, Cas writhing as best he could held down by cuffs and Sam’s body weight, but then the base was pressed neat against Cas’s ass, and Dean leaned back to get a good look.

“No idea how hot you look right now,” he said, and Sam carefully climbed off of Cas to stand behind his brother.

Yeah, definitely hot, impaled on something they’d bought for ten bucks in a junk shop, all tied down and helpless to stop them shoving it in him.

“But does he know what it is?” Sam said. He looked at Cas’s face, could see him breathing through having the object rammed inside him, and grinned. “Cas?”

“I...I’m not sure….”

“Tick tick,” Dean said. “If you wanna come, Cas, you gotta tell us. At least guess!”

But Sam knew Cas was too distracted to think, and that meant he didn’t get his reward tonight.

“I guess he doesn’t want to come after all,” he said to Dean.

Dean sighed, but he had a mischievous look about him as he grabbed the base of the candlestick and fucked the angel with it a few times as Cas whined and tried to pull away.

“Guess not. We’re gonna come, though, Cas. Sam, you wanna get the cage?”

As Dean finally pulled the candlestick out, and dumped it back in the basin, Sam took their favourite toy out of the top drawer and started to fasten it around the pleading angel.

He had Cas’s cock and balls tucked tight away by the time Dean had rolled a condom onto himself, despite Cas struggling and trying to pull away.

“Like I said,” Dean told him. “Naughty angel.”

Sam jerked himself off lazily, never coming close to coming, as Dean slid into Cas’s loose hole, and took the angel hard.

Cas’s breathing was coming in short, harsh gasps, his chest heaving as Dean took his pleasure and then slumped forward with a groan as he came.

As he pulled out, he pinched Cas’s inner thigh, hard. “Don’t think you’re getting off with a punishment, angel,” he warned.

Sam had put on a condom by the time Dean was done, and studied the angel thoughtfully before approaching.

“Can you hold his legs up and out of the way?”

Dean gave him a puzzled look, but straddled Cas as Sam had earlier, and undid his ankle cuffs so he could slip his hands under Cas’s knees and pull them up.

It gave Sam the perfect view of Cas’s ass, and more, and he spent the next few minutes delivering the threatened spanking, until the skin was cherry red and Sam was sure Cas would have come all over himself if not for the cage.

Dean looked steady enough, so Sam knelt facing him and pushed inside the helpless angel.

Cas almost shrieked as every thrust of Sam’s put pressure on his poor, reddened ass, but never once did he say the word that would get them to stop, and they’d both gotten pretty good at reading when he wanted to safeword out but wouldn’t for whatever reason.

He wasn’t there yet, and then Sam came, hard enough to turn every muscle in his body taut, before he pulled out and sank back onto his heels.

Dean climbed carefully off the angel, and then he and Sam removed the blindfold, the cuffs, and settled Cas between them.

He looked dazed, and almost...affronted. “What was that,” he muttered, sagging into their arms.

Sam stroked his chest, soothing him, while Dean grabbed a bar of chocolate from the bedside unit and broke a chunk off.

He slipped it between the angel’s lips, watched Cas chew it slowly.

“Later,” Sam said. “We’ll show you later. Did you like it?”

“I haven’t decided yet,” Cas said, giving the two of them a sharp look. ‘But you both enjoyed yourself.”

Sam watched the angel glare at the thing that had prevented him from coming, and reached down to remove the device.

Dean wrapped his arms around Cas, holding him still as Sam jerked him off slowly, building him towards the edge, held him there for a moment, and then took Cas into his mouth.

That was it, and Cas came with a desperate groan, and Sam swallowed everything he had to give.

“You are both evil,” the angel accused, as Sam settled next to him again. “And I should probably be offended, _Dean_ , that you haggled over ten bucks for something you intended to stick inside me.”

Dean’s mouth dropped open, and Cas grinned.

“Your thoughts carry.”

“You knew,” Sam said, and playfully poked Cas in the ribs, prompting the angel to hiss and pull away.

“I wasn’t about to ruin your fun.”

Sam kissed him, and then pulled the blanket up over the three of them. 

Maybe it was Dean who was due a spanking, but that was for when they woke up.


End file.
